Acylhydrazide Schiff bases: DPPH radical and superoxide anion scavengers

Medicinal Chemistry

Volumn 8, Issue 4, 2012, Pages 705-710

  Khan, Khalid Mohammed ^a   Taha, Muhammad ^a   Naz, Farzana ^a   Siddiqui, Salman ^a   Ali, Sajjad ^a   Rahim, Fazal ^a   Perveen, Shahnaz ^b   Choudhary, M Iqbal ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b PCSIR LABORATORIES COMPLEX   (Pakistan)

Author keywords

Acylhyrazide Schiff bases; Antioxidant; DPPH scavenger; Superoxide anion scavenger

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; GALLIC ACID PROPYL ESTER; SCAVENGER; SCHIFF BASE; SUPEROXIDE;

ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; IC 50; IN VITRO STUDY; IN VIVO STUDY; PRIORITY JOURNAL;

BIPHENYL COMPOUNDS; FREE RADICAL SCAVENGERS; HYDRAZINES; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; PICRATES; SCHIFF BASES; SUPEROXIDES;

EID: 84863768768     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340612801216111     Document Type: Article

References (46)

1. Khan, K. M.; Khan, M.; Ali, M.; Taha, M.; Rasheed, S.; Perveen, S.; Choudhary, M. I. Synthesis of bis-Schiff Bases of isatins and their antiglycation activity. Bioorg. Med. Chem., 2009, 17, 7795-7801.
2. Raman, N.; Raja, J. D.; Sakthivel, A. Synthesis, spectral characterization of Schiff base transition metal complexes: DNA cleavage and antimicrobial activity studies. J. Chem. Sci., 2007, 119, 303-310.
3. Panneerselvam, P.; Rather, B. A.; Reddy D. R. S.; Kumar N. R. Synthesis and anti-microbial screening of some Schiff bases of 3-amino-6, 8-dibromo-2-phenylquinazolin-4 (3H)-ones. Eur. J. Med Chem., 2009, 44, 2328-2333.
4. Khan, K. M.; Ambreen, N.; Hussain, S.; Perveen, S.; Choudhary, M. I. Schiff bases of 3-formylchromone as thymidine phosphorylase inhibitors. Bioorg. Med. Chem., 2009, 17, 2983-2988.
5. Puchtler, H.; Meloan, S. N. On Schiff bases and aldehyde-Fuchsin: A review from H. Schiff to R. D. Lillie. Histochemistry, 1981, 72, 321-332.
6. Khan, K. M.; Ahmad, A.; Ambreen, N.; Amyn, A.; Perveen, S.; Khan, S. A.; Choudhary, M. I. Schiff bases of 3-formylchromones as antibacterial, antifungal, and phytotoxic agents. Letters in Drug Design and Discovery, 2009, 6, 363-373.
7. Chohan, Z. H.; Pervez, H.; Rauf, A.; Khan, K. M.; Supuran, C. T. Antibacterial cobalt (II), copper (II), nickel (II) and zinc (II) complexes of mercaptothiadiazole-derived furanyl, thienyl, pyrrolyl, salicylyl and pyridinyl schiff bases. J. Enzym. Inhibit. Med. Chem., 2006, 21, 193-201.
8. Chohan, Z. H.; Pervez, H.; Rauf, A.; Khan, K. M.; Maharvi, G. M.; Supuran, C. T. Antibacterial and antifungal mono and di-Substituted symmetrical and unsymmetrical triazine derived schiff bases and their transition metal complexes. J. Enzym. Inhibit. Med. Chem., 2004, 19, 161-168.
9. Kabeer, A. S.; Baseer, M. A.; Mote, N. A. Synthesis and antimicrobial activity of some Schiff bases from benzothiazoles. Asian J. Chem., 2001, 13, 496-500.
10. Tarafder, M. T.; Kasbollah, A.; Saravan, N.; Crouse, K. A.; Ali, A. M.; Tin, O. K. S-Methyldithiocarbazate and Its Schiff bases: Evaluation of Bondings and Biological Properties. J. Biochem. Mol. Biol. Biophys. 2002, 6, 85-91.
11. Chohan Z. H.; Arif. M.; Shafiq, Z.; Yaqub, M.; Supuran, C. T. In vitro antibacterial, antifungal & cytotoxic activity of some isonicotinoylhydrazide Schiff bases and their cobalt (II), copper (II), nickel (II) and zinc (II) complexes. Enzyme Inhib. Med. Chem. 2006, 21, 95-103.
12. Guo, Z.; Xing, R.; Liu, S.; Zhong, Z.; Ji, X.; Wang, L.; Li, P. Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan. Carbohydra. Res. 2007, 342, 1329-1332.
13. Samadhiya, S.; Halve, A. Synthetic utility of Schiff bases as potential herbicidal agents. Orient. J. Chem., 2001, 17, 119-122.
14. Kaplan, J. P.; Raizon, B. M. New Anticonvulsants: Schiff bases of γ-aminobutyric Acid and γ-aminobutyramide. J. Med. Chem., 1980, 23, 702-704.
15. Verma, M.; Pandeya, S. N.; Singh, K. N.; Stables J. P. Anticonvulsant activity of Schiff bases of isatin derivatives. Acta Pharm., 2004, 54, 49-56.
16. Nawrocka, W. P.; Sztuba, B.; Drys, A.; Wietrzyk J.; Ietrzyk, J.; Kosendiak, J.; Opolski A. Synthesis and antiproliferative activity in vitro of new 2-aminobenzimidazole derivatives. Part 3 [1]. Reactions of 2-arylideneaminobenzimidazole with selected 1, 3-diketones. Polish J. Chem., 2006, 80, 279-287.
17. Küçükgüzel, S. G.; Mazi, A.; Sahin, F.; Öztürk, S.; Stables, J. Synthesis and biological activities of diflunisal hydrazide-hydrazones. J. Eur. Med. Chem., 2003, 38, 1005-1013.
18. Popp F. D. Potential anticonvulsants. IX. Some isatin hydrazones and related compounds. J. Heterocycl. Chem., 2009, 21, 1641-1645.
19. Loncle, C.; Brunel, J. M.; Vidal, N.; Dherbomez, M.; Letourneux. Synthesis and antifungal activity of cholesterol-hydrazone derivatives. Eur. J. Med. Chem., 2004, 39, 1067-1071.
20. Lima, P. C.; Lima, L. M.; da Silva, K. C. M.; Léda, P. H. O.; de Miranda, A. L. P.; Fraga, C. A. M.; Barreiro, E. J. Synthesis and analgesic activituy of novel N-hydrazones and isosters, derived from natural safrole. Eur. J. Med. Chem., 2000, 35, 187-203.
21. Leite, L. F. C. C.; Ramos, M. N.; da Silva, J. B. P.; Miranda, A. L. P.; Fraga, C. A. M.; Barreiro, E. J. Synthesis and analgesic profile of novel N-contianing hetrocylic derivatives: arylidene 3-phenyl-1, 2, 4-oxidiazole-5-carbohydrazide. Il Farmaco, 1999, 54, 747-757.
22. Melnyk, P.; Leroux, V.; Sergheraert, C.; Grellier, P. design, synthesis and in vitro antimalarial activity of an acylhydrazone library. Bioorg. Med. Chem. Lett., 2006, 16, 31-35.
23. Bedia, K.-K.; Elçin, O.; Seda, U.; Fatma, K.; Nathaly, S.; Sevim, R.; Dimoglo, A. Synthesis and characterization of novel hydrazidehydrazones and the study of their structure-antituberculosis activity. Eur. J. Med. Chem., 2006, 41, 1253-1261.
24. Cunha, A. C.; Figueiredo, J. M.; Tributino, J. L. M.; Miranda, A. L. P.; Castro, H. C.; Zingali, R. B.; Fraga, C. A. M.; de Souza, M. C. B. V.; Ferreira, V. F.; Barreiro, E. J. Antiplatelet properties of novel N-substituted-phenyl-1, 2, 3-triazole-4-acylhydrazone Derivatives. Bioorg. Med. Chem., 2003, 11, 2051-2059.
25. Terzioglu, N.; Gürsoy, A. synthesis and anticancer evaluation of some new hydrazone derivatives of 2, 6-dimethylimidazo[2, 1-b]-[1, 3, 4]thiadiazole-5-carbohydrazide. Eur. J. Med. Chem., 2003, 38, 781-786.
26. Greenfield, R. S.; Kaneko, T.; Daues A.; Edson, M. A.; Fitzgerald, K. A.; Olech, L. J.; Grattan, J. A.; Spitalny, G. L.; Braslawsky, G. R. Evaluation in vitro of adriamycin immunoconjugates synthesized using an acid-sensitive hydrazonelinker. Cancer Res., 1990, 50, 6600-6607.
27. Caffrey, C. R.; Schanz, M.; Nkemgu-Njinkeng, J.; Brush, M.; Hansell, E.; Cohen, F. E.; Flaherty, T. M.; McKerrow, J. H.; Steverding, D. Screening of acyl hydrazide proteinase inhibitors for antiparasitic activity against Trypanosoma brucei. Int. J. Antimicrob. Agents, 2002, 19, 227-231.
28. Bernardino, A. M. R.; Gomes, A. O.; Charret, K. S.; Freitas, A. C. C.; Machado, G. M. C.; Canto-Cavalheiro, M. M.; Leon, L. L.; Amaral, V. F. Synthesis and characterization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity. Eur. J. Med. Chem., 2006, 41, 80-87.
29. Küçükgüzel, S. G.; Rollas, S. Synthesis, charachterization of novel coupling products and 4-arylhydrazone-2-pyrazoline-5- ones as potenial antimycobacterial agents. Il Farmaco 2002, 57, 583-587.
30. Sawada, Y.; Yanai, T.; Nakagawa, H.; Tsukamoto, Y.; Tamagawa, Y.; Yokoi, S.; Yanagi, M.; Toya, T.; Sugizaki, H.; Kato, Y.; Shirakura, H.; Watanabe, T.; Yajima, Y.; Kodama, S.; Masui, A. Synthesis and insecticidal activity of benzoyl-N-(tert-butyl) benzohydrazide: part 3. Modification of N-tert-butylhydrazine moiety. Pest Manag. Sci., 2003, 59, 49-51.
31. (a) Khan, K. M.; Shujaat, S.; Rahat, S.; Hayat, S.; Atta-ur-Rahman; Choudhary, M. I. β-N-Cyanoethyl acyl hydrazide derivatives: A new class of β-glucuronidase inhibitors. Chem. Pharm. Bull. Jpn., 2002, 50, 1443-1446
32. (b) Gürkök, G.; Coban T.; Suzen, S. Melatonin analogue new indole hydrazide/hydrazone derivatives with antioxidant behavior: synthesis and structure-activity relationships. J. Enzyme Inhib. Med. Chem. 2009, 24, 506-515.
33. Rada, B.; Leto, T. L. Oxidative innate immune defenses by Nox/Duox family NADPH oxidases. Contrib. Microbiol. 2008, 15, 164-187.
34. Tarpey, M. M.; Wink, D. A.; Grisham M. B. Methods for detection of reactive metabolites of oxygen and nitrogen: In vitro and in vivo considerations. Am. J. Physiol. Regul. Integr. Comp. Physiol. 2004, 286, R431-R444.
35. Ravanat, J.-L.; Sauvaiga, S.; Caillat, S.; Martinez, G. R.; Mederiros, M. H. G.; Di Mascio, P.; Favier, A. Singlet Oxygen-mediated damage to cellular D N A determined by the comet assay associated with DNA repair enzymes. Bio. Chem. 2004, 385, 17-20.
36. Bolann, B. J.; Ulvik, R. J. Release of iron from ferritin by xanthine oxidase. Role of the superoxide radical. Biochem. J., 1987, 243, 55-59.
37. Chamulitrat, W.; Mason R. P. Lipid peroxyl radical intermediates in the peroxidation of polyunsaturated fatty acids by lipoxygen. J. Biological. Chem. 1989, 264, 20968-20973.
38. Yildiz, G.; Demiryurek A. T. Ferrous iron-induced luminol chemiluminescence: A method for hydroxyl radical study. J. Pharm. Tox. Methods 1998, 39, 179-188.
39. Radi, R.; Cosgrove, T. P.; Beckman, J. S.; Freeman, B. A. Peroxynitriteinduced luminol chemiluminescence. Biochem. J. 1993, 290, 51-57.
40. Henning, S. M.; Niu, Y.; Lee, N. H.; Thames, G. D.; Minutti, R. R.; Wang, H.; Go W. V. L.; Heber, D. Bioavailability and antioxidant activity of tea flavanols after consumption of green tea, black tea, or a green tea extract supplement. Am. J. Clin. Nutr., 2004, 80, 1558-1564.
41. Levine, G. N.; Frei, B.; Koulouris, S. N.; Gerhard, M. D.; Keaney, J. J. F.; Vita, J. A. Ascorbic acid reverses endothelial vasomotor dysfunction in patients with coronary artery disease. Circulation 1996, 93, 1107-1113.
42. Schmidley, J. W. Current concepts of cerebrovascular disease and stroke, free radicals in central nervous system ischemia. Stroke, 1990, 21, 1086-1090.
43. Noland, R. C.; Woodlief, T. L.; Whitfield, B. R.; Manning, S. M.; Evans, J. R.; Dudek, R. W.; Lust, R. M.; Cortright, R. N. Peroxisomalmitochondrial oxidation in a rodent model of obesity-associated insulin resistance. Am. J. Physiol. Endocrinol. Metab., 2007, 293, E986-E1001.
44. a) Zia-ur-Rehman, M.; Choudhary, J. A.; Elsegood, M. R. J.; Siddiqui, H. L.; Khan, K. M. A facile synthesis of novel biologically active 4-hydroxy-N'-(benzylidene)-2H-benzo[e][1, 2]thiazine-3-cabihydrazide-1, 1dioxies. Eur. J. Med. Chem., 2009, 44, 1311-1316.
45. Khan, K. M.; Ali, M.; Asma, A.; Perveen, S.; Choudhary, M. I.; Atta-ur-Rahman. Synthesis of arylidene barbiturate: A novel class of DPPH radical scavenging. Lett. Drug Design. Disc., 2008, 5, 286-291.
46. Ferda, C. Effect of rhus coriaria 1. (anacardiaceae) on superoxide radical scavenging and xanthine oxidase activity. J. Enzyme. Inhib. Med. Chem., 2003, 18, 59-62.